Experiences
by ChuckBlair08lover
Summary: What happens when Blair finds herself falling for her best friends older brother Chuck. "Life is a journey with problems to solve, lessons to learn, but most of all experiences to enjoy" AU/One-Shot.


**Characters:** Chuck/Blair

**Plot/Prompt: **AU, Blair's POV and possibly Chuck's POV.

"Like is a journey with problems to solve, lessons to learn, but most of all experiences to enjoy!"

**Description:** Chuck father Bart married Serena & Eric's mother Lilly when they were a lot younger. Serena was 6 & Eric was 4, also in this story I'm making Chuck actually around 2yrs older then what Serena & Blair would be, which would make him 8 at the time there families were combined. One other thing the kids will be in the adolescent stages in this. Just wanted to let everyone know that so there was no confusion there when reading the story.

**Disclaimer:** I do not own Gossip Girl nor their Characters, however I am truly and madly in love with no one other then Ed Westwick himself 3 our loving and ever so charming Chuck Bass!

* * *

Even though I always knew it was somewhat wrong it still never stopped me from obsessing over my best friends older brother. Even early on I seemed to be quit taken with him, between his dark hair & eyes not to mention his even darker personality. He always had this take on life that anyone would envy, he was fun, ruthless, always the life of the party no matter where he went, people always seemed to be drawn to him. Unfortunately that also meant plenty of girls too, it became quit obvious early on that I wasn't the only one who was mesmerized by him.

S.. are you sure its okay that were here?

B.. come on I already told you if Chucks going to throw a party at our house then yes its okay if we are here... I mean I do live here you know.

Yeah I understand that and all but still yet this party is for high school kids not Jr. High... I mean what if he gets mad or tries to throw us out?

He wont throw us out... besides even if he tries I got mom and Bart's number on speed dial and I'll just threaten to call them if he even tries to.

I hope your right S... because the last thing I want is the wrath of Chuck Bass brought down upon me.

Oh please... he's nothing compared to the raging bitch I've seen you be at times.

I haven't got the slightest clue what your talking about...

Really Blair... is it just me or is not half of the girls in our class terrified of provoking you.

Serena that's different... I mean dealing with Jr. High girls and guys are a lot different then dealing with the High Schoolers.

If you say so B... so anyways what do you think about my outfit?

"I see her twirl around, noticing automatically how much more older she looks compared to me between her super long legs to her shiny blonde hair not to mention her bubbly personality that seems to draw people in. Ugh.. why did I have to look like such a little girl still yet" You look great S... you always look good unlike me who constantly looks like a short chubby little girl.

Blair... I swear I don't understand where you find yourself fat, I think your super cute and petite not mention you have some of the biggest doe eyes I've ever encountered!

That's just it Serena... I'm cute... not sexy, not hot, not even beautiful but cute. "rolling my eyes at her, why couldn't she get it while she was tall and had legs for days not to mention she always looked older for her age as were I never did I looked exactly what a 14 year old girl should look like.

Come on B... stop being so hard on yourself... you know your beautiful, if you wasn't then half of the girls in our class wouldn't be super jealous of you.

Ch'yeah... whatever S I'm not quit sure I would even call it jealous, I think terrified is more the word your going for there.

Still yet you are seriously being way to hard on yourself...

Well what do you expect you and I maybe only 14 but you look like a 16 year old already where I look just that 14... "I seen her slump down on her bed, great not only am I the empitamy of everything I hate but I also seem to be the one who sucks the fun out of everything." Look S maybe you right... how about lets get out there and have a good time. Mise well mingle with them now we wont have a choice next school year.

That's the spirit B... now before we go put on this dress right here. I know it will look fabulous with your skin tone.

"I look at the dress skeptically trying my best to find any kind of criticism possible but failed to do so, the dress itself was absolutely beautiful but yet it held a type of sexiness I was not use to wearing just yet. After slipping it on and once Serena had zipped it up I couldn't stop staring at myself in the mirror, for some odd reason it ignited a fire in me that I hadn't know was even there but then again it could be because the dress was red but It made me feel almost confident even which was a foreign thought to me all together. Between the top part that covered my breast which was black and went all the way down and covered my arms in the most beautiful delicate black lace to the Red silk fabric that met the black right under my breast that smoothed its way down to my upper thighs even I had to admit that I looked hot... not cute but Hot! Maybe this party wouldn't be so bad after all"

* * *

Thirty minutes into the party was all it took for me to loosen up a bit well that and the 2nd cosmo I was downing at the moment, but either way I found myself feeling lighter and smiling more even laughing at some idiot dancing around that clearly had way to many drinks already.

B come on lets dance!

S I don't kno... "only then she jerk me out into the small crowd who was dance already"

The whole time we were dancing I couldn't help but feel myself getting lost in the music, normally I would be terrified to dance the way I was but for some reason I found that I didn't care, tonight was mine and all I wanted was to get away, away from my element and do something crazy and outrageous for once. I had never really seen myself as some sexual goddess by no means but for some reason at that moment I felt just that. Looking around I noticed so many eyes upon us granted it could've been because Serena was behind me at that time hands on my hips while her and I grinded to the music getting lost in the fuzziness and beat of the music. But I couldn't help but smile even brighter knowing that I was having this effect of most of the boys there, high school boys to be exact! After the song ended we made our way back over to the bar for another drink, we were both laughing over the expressions of half the boys at the party. I found myself having such a wonderful time that I didn't even realize who I bumped into until it was already too late.

Oops sorry... "looking up into those dark eyes that I'd seen so many of times"

Waldorf "looking down at the petite girl before me" Looks like your enjoying yourself.

Uh ye ye yeah... "what in the hell is wrong with me going from being the sex goddess of the party to the stuttering fool"

Good, I'm glad you seem to be having a good time, now if you don't mind I need to speak with my sis. "turning my eyes to the tall blonde"

Chuck what exactly is it that you need to speak to me about? "crossing her arms"

Oh nothing really Serena other then the fact that I clearly told you what my plans were for tonight and yet here you are in the way as usual!

Last time I checked this was my house too... so I have ever right to be here plus who are you to tell me what I'm suppose to do anyways?

Yeah that's just it Serena... I'm the oldest so what I say goes, plus I told you yesterday what I had plans on doing and even asked if you would occupy yourself else where but yet here you are.

Get one thing correct Chuck just because your father married my mother doesn't mean that your the boss of me. And don't forget that I can make this all turn bad real quick.

Ohh threats... aren't we wearing our big girl panties tonight! "smirking at her" What are you going to do call mommy and daddy on me, if you do please don't leave out the part where you was practically whoring it up out on the dance floor not to long ago.

Your stupid Chuck... I wasn't whoring anything up, its called dancing and as for anyone being a whore around here that's clearly you!

Yeah keep telling yourself that sis... "just as I was about to say something else that's when I found myself interrupted"

Chuckie... what is taking so long

Its nothing Georgie... "rolling my eyes, she was seriously getting on my last damn nerve tonight" just talking to my sister and her friend.

Oh.. hey Serena hope he wasn't giving you a hard time... you know how Chuck can get sometimes.

After hearing the heated argument between Serena and Chuck I found myself wanting to get as far away from him as possible, the last thing I wanted was to crash Chuck's party plus I really didn't want him pissed at me for Serena failing to tell me that we was in fact not invited. So taking the situation at hand I decided that getting away from him would be the best thing for now.

Serena "I suddenly found myself speaking up" how about you and I go grab a bite to eat down at the 5th quarter or something, get out of here for a while. "when I seen her nod a yes I took that as my opportunity to grab her hand" Chuck sorry about earlier we will leave you alone now. "pulling her around with me to make our exit only to hear the one person I was hoping to avoid speak"

Well well... if it isn't little miss Blair Waldorf herself...

Turning around looking into the eyes of none other then Georgina Sparks, she was tall with sleek black hair and green eyes, this wasn't our first time meeting clearly, she was as mean and nasty as they come. Her and I had always had this profound hate for one another sense the first time we came into contact. Sixth grade for me and Eighth for her, right after I turned down her annoying little brother Alex Sparks to the Christmas Formal that year, she seemed to hated me ever sense that moment. I was surprised she just noticed me maybe I should have kept my mouth shut after all.

Georgina... "smiling back at her" how are things with you? "trying to make small talk, I see her smile that evil conniving grin of hers while wrapping her arms around Chucks shoulders"

Oh things have been great... Chuck sense when is it okay for 12 year olds to be at your parties? "she began to laugh"

Ugh... I knew it was coming, I was stupid to ever let Serena talk me into coming to this godforsaken party anyways. So what else was I suppose to do just let her laugh at my expense no there was no way I could do that... so I launched into action.

Funny Georgie... "rolling my eyes" You know how old I am, I mean I am the same age as your annoying grungy little brother after all!

Oh yeah that's right... I swear I never knew what Alex seen in you or why he even obsessed over you as long as he did. Clearly everyone here see's your nothing but a little short frigid bitter bitch that thinks she better then everyone else when clearly she not!

Yeah that's exactly what I think Georgina... Look I cant help it that I'm shorter then most but at least I'm not some graceless vindictive slut like you! "seeing her eyes grow larger I knew I was pissing her off even more, but I also noticed someone else's face too who seemed quit amused with my choice of words too. It was Chuck he was smirking but yet grinning slightly at me.

Whatever little girl... please go on your way I would hate to embarrass you in front of all these people.

Before I could say anything back, it was Chuck who spoke up this time.

Georgie calm your shit... "looking to the psycho next to me before turning my eyes to the petite brunette" Waldorf your welcome to stay... you don't have to leave. "turning my eyes to Serena" Sis just stay out of my way got it? "seeing her nod I took it then proceeded to walk away" You girls stay out of trouble now don't get to wild "smirking while taking my leave"

* * *

After what transpired earlier I found myself drinking a bit more to calm my nerves, not only from Georgina's clear hatred for me but also I was finding myself feeling giddy for some reason. I just kept replaying the words Chuck spoke earlier in my head over and over seeing him smiling at me during my insults thrown at that slut, the look of amusement in his eyes but also possibly a hint of admiration in them too almost as if he agreed or approved of what I said. Looking around that's when I spotted Chuck and his friend Nate setting on the couch with Georgina and 3 other girls all around them. Already I could tell they had more to drink then they did before they were also passing around what looked to be a joint while one girl took a drag off of it I noticed Chuck lighting another one. I had never tried pot or any kind of drugs for that matter the only thing I ever did was had a few cocktails here and there but never as much as I had tonight, already I could feel myself becoming a bit more tipsy. Dancing with Serena on the dance floor while noticing all the boys eyes that was once upon us again. That is when I noticed that one of those boys eyes was none other then Chuck himself.

Blair this has been such an awesome party so far do you agree "yelling over the music"

Oh definitely! "truly it was other then my run-in with Georgie earlier, looking over to the couch that Chuck was just setting on to find it empty" Its going to be one to remember that's for sure! "just then I seen Nate come behind Serena and wrap his arms around her shoulders and pull her back to him"

How's it going Rena...

Natie! "squealing his name" I was wondering if you was ever going to talk to me.

Of course you know I would... "he smiled his signature pearly whites her way" Waldorf I heard you made it out alive from under Georgies wrath?

You know it! "smirking back at him, looking at Serena who was clearly in love with her brothers best friend and who had been for a long time. I still had to here all the time from her how hot he was and how he would openly flirt with her all the time" She doesn't scare me... you of all people should know that.

I believe it... your just about as vicious as Chuck is. "laughing"

Speaking of Chuck where is that brother of mine anyways?

Right here of course.. "walking up behind the petite brunette"

Aye man... I was wondering if you were going to follow me over here or not.

Yeah.. I just had to get rid of the trash first... "Smirking at Nate, knowing he knew what I meant" Waldorf its nice to see you again.

Likewise! "smiling up at him, but before I could say anything else that's when I felt his arms wrap around me and pull me back to him. Startled at first as to feeling his body so close to mine. Now let me have you know that this was not the first physical contact between him and I, through the years he would constantly tease me or playfully pull at my hair or poke at my sides even making it a purpose to pick me up and throw me into the pool during the summer at the Hamptons but all those times it had been innocent but now the way his hands seemed to circle my waist felt like anything but innocent. But it also felt right, I would be lying if I said I hadn't ever found him attractive because I had & loved when he would give me even the slightest bit of attention. But right now feeling him moving my body with his back and fourth to the music was just out of this world almost more then I could handle but that doesn't mean I was prepared to stop.

Dance with me "he whispers into her ear"

Okay but only if your sure you can keep up "having him whisper in my ear sent a tingle down my spine id never had before, but not wanting to act like some loved crazed girl I decided to use our everyday banter with him"

Oh I can keep up Waldorf the question is can you keep up with me?

I'm pretty sure... I can "turning my face back towards him and smirking"

Pretty sure huh... I hope your positively sure! "straining out the last two words from my mouth in an almost seductive way"

I felt his hands cup both of mine bringing my arms up into the air pulling them back were they fell slightly behind my head then I felt him wrap my hands around his neck it was then he slid his hands down the length of my arms and onto my sides just barely grazing past the sides of my breast but not touching them where he finally landed on my hips pulling and pressing his hands into them he began to push himself almost forcefully behind me. It was the first time that I had felt another's hands all over me like his was at that moment the sensual way he glided his hands along me arms and down my sides just seconds ago seemed almost effortlessly to him like he had done it numerous of times, which when I think about it I'm sure he has but to me it was something entirely new once the music picked back up its pace that's when I felt him circle my waist pulling me back to him even harder before dipping me down in front of him. He then proceeded to grind on me even more I found myself instinctually bending my knees and moving right along with him taking in more of his feel and body then I'd ever done before. Swiping my hair over to side so I could turn to look at him I don't know why but I just wanted to see his face at that moment when I turned to look at him I found him smirking right at me but his eyes seemed like he was liking this just as much as I was. Resting my hands on my knees I began to move more forceful causing him to tighten his grip around me all at once.

I had been completely lost in the moment that I didn't even see the slut who walk up behind him until I found myself almost face planting that exact moment. Quickly I stuck both my hands out to the ground but then felt another set of hands grab for them looking up to see Nate standing there holding not only my weight but also the weight of Chuck too who had been pushed in the back which caused us to fall forward. After straightening myself back up it was then I noticed the absent of Chucks hands on me, I don't know why it bothered me but for some reason I missed his body on mine. Turning around that's when I seen his eyes on me.

Blair are you okay? "he asked"

Uhh.. Yeah I think so.. "it was so weird hearing him call me by my first name not that he hadn't before but Waldorf was what I was use to from him anyways" Are.. are you?

Yeah.. I'm fine... "but before I could say anything else that when I felt a slight push again turning around I found it was the trash I thought I'd put out earlier but I guess I was mistaken" What the hell Georgie

Yeah that's what I'd like to know Chuck... what the hell are you doing dancing with her?

The last time I checked Georgie I don't belong to anyone so I can dance with whoever the fuck I want! "this psycho was driving me insane"

Oh so you think you can just invite me over here and fuck me then be done with me huh?

Pretty fucking much... I done told you to leave didn't I... or did you not get the hint.

Chuckie... "whining out his name" don't be mean... I know what you like... why don't we go to your room for a little more fun?

Umm... how about you get your ass out of my house for the second time now. "rolling my eyes at her who the fuck did she think she was" I don't do seconds you know that... You knew that before you climb on my dick so please see yourself out.

I cannot believe you... seriously Chuck your going to pass off on a sure thing for what... "looking over to the petite brunette" A frigged virgin who clearly wont put out not to mention is fourteen Chuck or did you forget?

Georgie shut the hell up already... Her and I were just dancing which has nothing to do with you... last I checked I wasn't propositioning her for sex anyways.

Oh weren't you, everyone here could practically see you humping her ass Chuck... "turning to the brunette" And you... what happened to little miss pristine Blair who would never let a guy get that close. You were practically eating it up just now.

GEORGIE! end it now! I told you I was threw with you hours ago & yet here you are acting like some jealous crazed ex girlfriend, which by the way would never happen.

Whatever Chuck... I will leave but just so were clear don't come begging me for anything else because it will be a NO!

No worries there Georgina... besides I don't beg anyone... they beg me so don't forget that you psycho bitch! now LEAVE!

After what transpired once again from the crazy bitch Georgina, Chuck and Nate ended up returning to the couch where they smoked another joint before Chuck announced to everyone that the party was over and for everyone to be making their leave. Once everyone was gone Serena and I went back to her room where I changed into something much more comfy. I found myself hating Georgina more then I did before, why did that slut have to ruin Chuck and I's time for I was genuinely enjoying dancing with him but after her little display Chuck had practically turned around and ignored me after that, I just hope I hadn't done anything to make him mad at me, or maybe I'm just overthinking this whole situation. Laying there that night listing to a snoring Serena next to me I began to rehash the whole party from the beginning to the end, closing my eyes I found myself hoping that tonight wouldn't be our last encounter.

* * *

Five days went by sense I had spoken to him, even that morning after the party he still seemed to keep himself hidden it wasn't till after I was packing my over night bag up and heading towards the elevator waiting for it that I seen him but even then it was brief getting into the elevator I seen his eyes catch mine were I smiled at him on instinct but I noticed he didn't smile back watching the doors shut I knew then that whatever happened between us that night clearly wasn't going to happen again. Who was I kidding to seriously think anything of it anyways, he was probably high and drunk that's probably the only reason why he was dancing with me like that. Sense that morning I found myself making excuse after excuse to Serena for why I couldn't come over I hated lying to her but I seriously didn't know if I could handle being around Chuck at the moment especially sense he took to hating me now. But after Serena had missed two days of school that was when the teacher asked me to dropped her work off at her house so she wouldn't fall behind I immediately complied. As I was riding the elevator up to the top penthouse suite I couldn't help but feel overly nervous. Once the doors opened I peered my head in their home to find no one in eyes view so I stepped out and walked into the living room.

Serena... "I yelled while looking around I found no one in the living room nor the kitchen.. I then walked into the dinning area but no one again. I began to walk down the long hallway that led to the bedrooms once at her door I started to knock"

Serena it.. its Blair... "still no answer" Mr. Davidson sent me with some of your assignments where you have missed school... "nudging the door open I looked inside to find her bed perfectly made her light off and no one in sight so I walked further in and laid her books down on the desk. Walking over to her on suite bathroom to find nobody insight" Well this is awkward... "I mostly said to myself, it felt weird being in someone's house when it seemed that nobody was even there. I decided to get out of there quick turning and leaving her room I made my way back down the hallway but before I could leave it was then I heard the ding of the elevator.

I looked up hoping to see Serena or at least someone so I could tell them why I stopped by but my eyes found no one other then Chuck himself except he didn't seem to notice me and he also seemed to not be alone either. I watched him pull what looked to be a redheaded girl into the living room where he threw her down on the couch and began to unbuckle his pants it was then that I noticed I was in clear view for either one of them to see I began to panic but quickly dash towards the kitchen and bent down behind the bar the separated the kitchen from the living room, hoping that it hid me enough from anyone's view.

While staying huddled down on my knees I couldn't help but be intrigued by some of the noises I was hearing, I soon found myself peering my head over the side of the bar while still on my knees, it was there that I had the perfect view of whatever activities they were currently in. I seen Chuck kissing the girl almost aggressively and heard the girl moan into his mouth, he then started nipping at her jowl going down to her breast where evidentially she had already discarded her shirt It was then that I seen him take one of her nipples into his mouth and began to suck and circle his tongue around them, giving both of them attention. He then bit down on them eliciting a higher pitch moan from the girls mouth.

I don't know why watching him was making me feel almost excited, but I began to feel heated too and couldn't help it when my own hand began to rub and message over my breast almost trying to mimic what I had seen him do moment before I watched his hands push up her skirt to reveal her panties it was then he pushed them to the side and began to plunge his fingers in and out of her. I too found my hand traveling down and disappearing under my school uniform skirt where I began to explore my own body down there, I was hesitant at first never had I ever touched myself like I was at this exact moment but then again never had I'd been so turned on either like I was right now so I finally pulled the side of my panties over and pushed one perfectly manicured finger into my own hot core which I found was extremely wet.

Watching Chuck moving his fingers in and out almost expertly, it was then that I seen him start to rub further up on her with his thumb which cause the girl to squeal and moan even more.

Ohhhh... Ohhh... Yes... YES CHUCK! "screamed the girl"

You like that don't you... "he answered back while applying more pressure"

I started to move my finger in and out even faster watching Chuck pleasure this girl and hearing her moans and his voice only served to turn me on even more. It was then I seen him back away from her a bit to reach for something on the floor. Once he opened it that was when I noticed what it was, he then pulled himself out from his boxer briefs but was almost to quick at sliding the condom on before I manage a good look at his manhood in question it was then I seen him plunge himself into the girl forcefully and hard. Not holding anything back he moved in and out of her enticing loud moans that could be heard all through the house, I watched the girls head fall back and her body arch into him even more.

Yes.. Yes... Yes Chuck... that feels so goooood!

You want it harder baby...

Yes.. HARDER... HARDER CHUCK!

I watched him pull back and then plunge into her with more force then before, repeating this over and over until he was moving so fast and hard that the girls breast were practically bouncing up and down with force from the impact of Chuck. I began to go harder and faster mimicking him moving in and out of her. It was then that I heard the girl scream and saw her began to shatter before my eyes which caused a slight moan to gasp from my lips too clamping my hand over my mouth I looked to them again seeing the girl still moaning and Chuck still going made me think good they didn't hear me. Clearly this girl reached whatever it was she was needing reverting my eyes back to Chuck it was then I seen him push himself a few more time before he too stilled and let out a slight noise. After that he pulled himself from her and pulled the condom off to tuck himself back in his boxers he buckled his pants back up and bent down and retrieved her shirt only to toss it to her moments later. He then told her he was going to the bathroom and handed her a few bucks and told her that she could get a cab with that.

* * *

Crawling myself over to the pantry the was mere feet away I back myself up into the tiny shelf that laid on the bottom I guess being petite had its advantages, it was then that I seen Chuck walk by heading towards the bathroom, thinking to myself good once this girl gets out of here then I will too. I waited for what seemed like forever and finally I heard the girl gathering her purse and making her way to leave once I heard the elevator doors shut it was then I started to crawl out from where I was hiding but before I could make my way completely out and off the floor and into the elevator Chuck walked right back into the living room. which startled me and caused me to back into the shelf again only this time I hit my head causing a few things to fall over me and into the floor. Squeezing my eyes shut I knew it was already to late I heard him walk into the Kitchen knowing good and well that he seen me.

What the fuc... "walking into the kitchen it was then I seen a petite little brunette down on her hands and knee's halfway in the pantry and halfway out, her eyes was squeezed shut which made me chuckle slightly it was like she thought if she closed her eyes it would somehow make her invisible" Waldorf? is...is that you?

Hey Chuck... yeah its me "gaining enough courage to look up at him finally"

What the hell are you doing down there? "walking closer to her extending my hand out to help her up"

I... I was just stopping by to drop some of Serena's school work off that she's missed this week that's all "reaching for his hand he pulled me up to stand before him"

Well Serena's not here... Her, Eric, Lilly & my Father flew up to Maine yesterday for some type of meeting for Bass Industries. There not set to return till tomorrow.

Oh, well I should be going then... "turning I then went into the living room and gathered my bag and slid it back on my shoulder, how in the world I forgot about it being in the living room was beyond me"

Waldorf wait... "looking at her standing there it was then I noticed the bag hanging on her shoulder the same bag I moved off the couch moments before pushing the redhead down on it. Wait if that's the case then she was here the whole entire time, I guess that explains why I found her hiding in the kitchen on the floor then."

Yeah.. "looking up to find him standing before me, I swear could things get anymore weird, from not speaking or seeing each other for 5 days to this" Did.. did you need something?

How long have you been here? "I couldn't help but find her fiddling with her strap to her bag funny but it was clear she was nervous which only seemed to make this much more fun."

I...I just told you, I came by to drop some things off for Serena that's all. "oh my god... had he realized that I was here the whole time... stupid question I guess I was hiding in the kitchen and on the floor none the less"

I already know that... "smiling at her" but that wasn't the question... I asked you how long you've been here? "stepping closer to her"

Long enough... "swallowing hard as he stepped closer"

So you was here before I got here then? "watching her nod a yes" did you see what just happened in here with that girl? "when she didn't nod or say anything I knew she had to of seen something so I asked her again, this was rather amusing in some ways" Blair, did you?

Yes "I whispered, before looking up at his eyes which instantly found mine" I... I didn't mean to Chuck, I was coming back from Serena's room getting ready to leave and that's when you and that girl came out of the elevator and into the living room. "I began to speak up with more speed then I normally do stumbling over a few words here and there" I swear it..

Chill Waldorf its okay... I'm not mad at you... I just hate that you had to witness that whole thing. "smirking at her trying my best not to laugh at her nervous explanation for why she was here"

Its okay really... It wasn't even that bad... "shit did I seriously just say that out loud" I... I mean... I mean... "ugh just shut up already"

So you think it wasn't that bad huh... what about it was good exactly? "I know I shouldn't have pushed it but I couldn't help it she peaked my interest with what she said, was she into watching me or something I just had to find out now"

Well uh...uh it was different. "why was he asking me this right now"

Different... how so? "I could clearly see I was making her more nervous then before so I decided to reassure her that all was fine" Look Blair its fine okay.. there's nothing to be nervous about... you know me I know you so its not even that big of a deal.

No its not that Chuck its just well.. "hearing his words seemed to help calm me down a bit so I decided to be truthful with him" I have never seen anything like that before... I mean well it was so intense and... and... well quit amazing I suppose.

Amazing... "I began to smile at her, for some reason I found myself hanging on every word she said"

Yeah.. I've never seen such pleasure like that in my entire life.

All I see... "hearing this from her made me want to know more" Have you ever had an orgasm before Blair?

Uh no... never like that, I guess that's why it intrigued me. " I seen him stare into my eyes even more" I mean I'm a virgin obviously, I've only kissed guys before and that's been it.

Do you mean to tell me that no one had never touched you like that before? "watching her nod a no, which made me ask her the next question" What about yourself, have you ever touched yourself like that?

I...I have, but it isn't something I ever really do or would have done anyways.

I'm not sure I understand you there... you have touched yourself but yet its not something you would have done?

I just mean that I've only did it once.

And did you find yourself liking it... did it bring you to have an orgasm?

No... I didn't, no where in comparison to what that girl was having.

I see... so you have never experienced what it feels like to have an orgasm. "I couldn't help but find that this turned me on, I mean I had practically grew up with this girl I guess I just figured that at least she had been fingered or something like that because Lord knows Serena was no innocent thing. But I found myself suddenly intrigue by her even more then I had been before, granted I'd always found her to be beautiful but lately she seemed to become more and more sexy then I'd ever noticed before which was why I found myself dancing and grinding on her at the party but then after Geogrie called me out it made me freak out a bit which caused me to stay away from her and ignore her but now I wasn't sure how much longer I could keep doing that."

No... never have I felt anything remotely like that. "wondering what I was getting myself into and why I was even answer his questions like I was but for some reason I couldn't stop starring at him he seemed to be deep in thought for some reason"

Well maybe you should change that.. because everyone should know what it feels like. "for some reason I knew what I was about to suggest was crossing the line but it still didn't stop the words from escaping my mouth" Or maybe I could change that for you even... if you want to that is.

What do you mean... that you could change that?

Blair I'm offering to give you your first orgasm... that's if you want to, I'm not about forcing anyone to do something they don't want but if you want to then I can bring you to that experience that you are talking about.

What exactly are you going to do to me... because I.. I want to keep my virginity... I mean I'm only 14 after all.

I get that Blair "laughing a bit" I'm not going to fuck you or anything but if you want me to then I'd like to finger you, I promise I will make it feel so good for you. Fingers only, it wont go any further then that. "watching her face, I noticed that what I was purposing seemed to be turning her wheels in her head"

I uh... Okay... "I couldn't believe I was actually agreeing to this but ever sense the party all I wanted was to feel him"

Are you sure... "still noticing her hesitation, clearly she was scared" I mean because if your not then we will forget about this whole thing.

NO... "I yelled almost loudly which caused him to looked somewhat amused at me" I mean... I want to.. I want you to make me feel this forbidden pleasure that everyone else has seemed to feel. I'm just scared a little that's all to what exactly its going to feel like.

There is nothing to be afraid of. "taking her bag off her shoulder and dropping it to the floor" Come on "grabbing her hand I began to pull her towards my room feeling her tense up a bit" Blair I promise its going to feel amazing, and if you want me to stop all you have to do is tell me.

* * *

Hearing his words only reassured me more so I began to walk with him to the very back bedroom that was his, I had been in here numerous of time in the past but never for what was about to take place, I don't know why but I found myself not only nervous but also excited to finally feel what an orgasm was suppose to feel like but knowing it was Chuck who was going to give me one made it that much better. Finally we walked into his room where he then told me to take a seat on his bed and get myself comfortable. After removing my uniform jacket and tossing it to the floor it was then that I heard music coming from his iPod stand it wasn't overly loud or anything but faint enough to know it was playing. I watched him walk into his closet to only return moments later changed into a pair of ball shorts only, starring at his chest I tried to figure out when it was that Chuck became so solid and detailed looking granted he had filled out a lot more over the last 2 years but still he looked really toned now which only seemed to turn me on even more. I watched him walk over to the bed were I instantly kicked off my heels completely forgetting to before.

Okay Blair again I tell you that If there is anything you don't like please tell me and I promise to stop. "It was then that I slid on the bed positioning myself over her"

Seeing him slide his body over mine and his eyes connected with mine, I seen him smile a reassuring grin before reaching out with his hand taking my face in it. His lips then connected in that moment, and we shared our very first kiss. My lips started to move against his by instinct. It was then I felt his tongue swipe against my lower lip which caused me part mine granting him access into my mouth completely. The moment his tongue met mine was the first time I had the chance to take in all that was Chuck and what he tasted like. Scotch & a hint of Mint, forever I would remember that taste.

Never had I ever felt such delicate lips, she kissed me with a softness yet yearning I hadn't experienced before which was saying something considering the source. As I slid my tongue into her mouth finding her tongue almost waiting for mine it was then that I first tasted what Blair actually tasted like. Sweet Cherry like almost, the taste was unlike any id had before. After our tongues dance with each others I heard her sigh into my mouth, I pulled back to look at her face. Seeing her breathing in and out feeling the air escape from her parted lips making its way on to mine it was then that I seen her dart out her little wet pink tongue which licked its way over her bottom lip before disappearing back into her mouth, it was clear this girl didn't know what kind of power she could hold over a guy. I couldn't help but wonder why it was my first time noticing how perfectly shaped her lips were they were full and pouty almost heart shaped like watching her part them even more and seeing her perfect white teeth peek through made me grasp under her chin lightly to tilt her face up towards me. Seeing her big doe brown eyes looking up at me it was clear she wanted more, sometimes looking into her eyes was like reading a book into her life they told you everything and yet nothing all at the same time.

Feeling his lips on me once again, I began to kiss him with more passion this time raising my hands and running my fingers almost effortlessly through his hair letting my nails glide through the softness. The things he could make me feel at this moment from just a kiss was crazy, I couldn't even begin to imagine what was to come. He then pulled away from my lips and begin sucking and nibbling on my earlobe. Moving from there down to my neck where he sucked gently for a few seconds which cause me to moan slightly from the sensation.

Blair, is it okay if I unbutton your shirt you don't have to take it completely off or anything. "Once I seen her nod a yes that's when my fingers begin to expertly run down the front till every button was undone" I'm going to get you a bit more relaxed before doing anything else okay, but for me to do that I'm going to remove your bra first okay, in which I will play with your breast before going lower. "seeing her nod, I looked into her eyes once again finding myself lost in those big pools of emotion, every feeling at this moment was something so unlike Chuck but I couldn't stop it from happening"

Pulling her shirt open it was then I got a better look at what was underneath, the small swells of her breast were peaking up slightly from her bra. Granted they wasn't huge by no means but they seemed to fit her perfectly. She had on a lace bra that was dark purple in color, which happened to be my favorite color. I then noticed it unclamped from the front which I always liked for the convenience purposes, after unclenching her bra it was then that I noticed her arms coming up shielding herself from my view.

Blair... you don't have to be nervous...

Chuck its not that... its just well you've seen a lot of breast and well what if you don't find mine to your liking.

That could never happen Blair... I swear now come on... "after watching her hesitantly remove her hands it was then that I was able to see them fully exposed"

Beautiful... simply beautiful Blair "and they were.. they seemed to be made perfectly for her, her breast while small seemed to be beautiful too, almost ghostly nipples that sported the perfect pink buds sticking up for me."

My hands began to message each breast squeezing softly pulling upward and pushing them back down making a circular motion with my hands which cause her to whimper slightly, it was then that I descended my mouth taking one of the dusky pink buds in where I began to suckle and lick with a eagerness yet tenderness that even I didn't know I possessed. Usually I was aggressive with my assault and quick too, but for some reason I found my self moving slowly and delicately with her almost wanting this to last. I felt her hands intertwined in my hair and her nails press into my scalp as if letting me know just how much she liked what I was doing after showing attention to each breast I moved back up and started to kiss her perfect pouty lips again before pulling back and looking at her once more.

Blair if your ready I'm going to move on down "she then kissed my lips lightly before nodding a yes"

Moving my hands down and over the swells of her breast, down her perfect flat stomach until I reached the top of her skirt, I decided to just push the skirt its self up towards her waist once I did that I seen her little purple lace panties that matched her bra from earlier, I couldn't help but take her body all in. She already had curves to her but was still small and petite like she had always been, she honestly had one of the most beautiful bodies already and she wasn't even grown completely yet it made me think what type of beauty she would one day be, & for some reason I found myself secretly thanking God that I was the first to ever touch her and bring her withering before me to know that it was me that was able to bring her such pleasure was starting to drive me crazy. Taking a deep breath regaining some of the control I had earlier.

Breathtaking Blair... you seriously have a beautiful body. "she smiled at me, taking in every word I professed to her. I began to run my hands on her upper thighs getting closer and closer to her forbidden box of pleasure, finally I began to rub my fingers over the outside of her panties. I ended up finding that they were already damp meaning she was already wet for me which only served to turn me on even more.

* * *

You sure? " I asked her before fully going in"

Yes.. I'm sure.

It was then that I pulled her panties completely down her legs and tossing them to the floor. Looking down at her like this spiked my excitement even more, it was like I was kid in my favorite candy store and I had just found my prized sweet, Her pussy seriously was a piece of art to me it looked like a peach almost or at least the shape anyways. My fingers soon found there own way down on her and I begin to slip one of my fingers between her slick folds feeling just how unbelievably wet and ready she was for me. Her pussy was pink as can be and it made me feel giddy once more knowing that I was the first person she granted access to touch her like this.

You are ready for me aren't you... "I couldn't help but get vocal" I promise this is going to feel amazing Blair.

I plummeted one of my fingers into her tight wet core which caused her to gasp, looking into her eyes I noticed they became instantly glazed over. I begin to move my finger in and out of her slowly until she seemed much more accustomed and comfortable with my efforts.

I'm going to add another finger now okay, so if it gets to be to much tell me... "it was then that I pushed both fingers into her tight core which was difficult at first but once she started to spread her legs for me it became a bit easier to push them completely and fully in which caused her to moan out loud.

OHHHHH... "it was then that I closed my eyes taking it all in, Chuck and his fingers inside me was almost too much, I was afraid because even earlier I had only used one finger but him using two and them being much more thicker and longer then mine seemed to feel much more amazing"

Does that feel good Blair? "as I begin to push in and out slowly moving my fingers slowly at first before picking up my speed a bit more, hearing her whimper and moan at each thrust was like music to my ears.

OHH...OHH... GOD YES... YEAH... YEAH... "I began to become more and more vocal with each thrust of his fingers it was becoming hard to bare and my body began to feel extremely hot, and things seemed to start feeling almost hazy.

I love hearing you moan Blair... you have no clue what your doing to me right now... watching your face faltered every time I plunge my fingers into that tight little pussy of yours... "putting emphasis on each word with a deeper faster push into each time."

The feeling of his hands, his body, his fingers, even his words that he spoke at that moment were beginning to drive me close to the end but it also caused me to scare away afraid of the unknown... of what could possibly happen or take place once I was there.

Let go Blair... "I then begin to finger her much more faster and harder then before, I also added my thumb into play as it started its assault on her perfect rounded clit moving in a circular motion that cause her to arch her body up before me.

UHHH...OHHH...GOD...OH MY... "I began to yell even louder the feel of his fingers pushing harder and faster then before and the sensation that his thumb seemed to be bringing me too was getting more then I could handle.

Come on Blair... let go... let go for me... you know you want too "I rubbed her clit harder and faster" Cum for me Blair... I want to feel you shaking all around me, I want to feel you spew your juices over me so I can suck my fingers clean... come on... give in to me Blair... Now! "I began to ignite much more force with each thrust into her until it happened I felt her body tense up before her head feel backwards and her eyes shut it was then she began to scream out in pleasure as she finally reach her peak and was over come with the feeling she had never experienced before, never in my life had I been more turned on then I was at this moment.

YEAH... YEAH... YEAH... OH MY GOD CHUCK... YESSSS... YESSS... CHUCK...CHUCK... "this foreign feeling that seemed to possess my body was so alien to me it was almost like I didn't know what to do with such pleasure and emotion. The few things I did know was that if this was what an orgasm was suppose to feel like then I needed to have them more often, another thing was who it was that was bringing me to such high pleasure was Chuck Bass. The way he could make me feel was out of this world, it left me desperately wanting him more.

I love hearing my name from your lips... watching your body shake feeling you vibrate against my fingers right now is an essence in itsself Blair. "after watching her ride out her first orgasm it was then that I withdrew my fingers from her pussy after feeling the gushing flow of her sweet liquid all over them, hearing her elicit a whimper from the loss of contact made me smile knowing that I had this effect on her. It was then that I brought my fingers up to my lips taking both fingers into my mouth and for the first time tasting what Blair Waldorf tasted like and what I found absolutely amazed me, it was sweet but still had a hint of something salty almost like an exotic fruit that was forbidden to eat which only made me suck my fingers even more until they were practically clean. I was never one to really indulge on eating a girl out but at this moment that's all I wanted to do... The taste of her only left me wanting more.

* * *

Chuckkk... "I managed to get out after finally opening my eyes after coming down from my mind blowing orgasm. I found him licking and suckling the same fingers that was once in me which seemed to fascinate me, I watched his eyes meet mine" What... are you doing? "I began to smile at him"

Tasting what Blair Waldorf is suppose to taste like... "he smiled back at me" Which is amazing by the way... seriously... "he smirked"

Well I'm glad you like the way I taste "laughing a bit at his antics while he continued to suck on his finger still yet" That... that was simply amazing Chuck... I don't even have words for what you just made me feel.

I'm glad I could be of assistance... "he smiled again before pulling his fingers from his mouth finally"

I am too I swear that felt nothing like it did earlier when I tried to do it to myself but with you it was simply amaz...

Earlier... "he looked at her then" As in earlier when I was with the redhead you mean?... "instantly remembering what she told me that she had only did it once" Wait so the first time you touched yourself was when I was well you know with that girl earlier...?

Ye... yes... "I managed to get out, why I was suddenly feeling embarrassed was beyond me considering what just took place between us"

That's so hot... your too beautiful you know that... "looking at her cheeks as they flushed red from embarrassment I couldn't help myself, I then crashed my lips against hers once more."

Tasting myself on his lips and tongue was another experience for me and something new to yet have happened, he was deepening the kiss even more and at first I couldn't understand why he even kissed me again, he pleasured me like he said he would shouldn't he be sending me on my way now. But before I could think to much on it his phone began to ring which he immediately ignored until it began to ring a second time, finally he sighed and pulled away letting out a groan that he was not happy to be interrupted.

Nathaniel... to what do I owe this pleasure... "ugh I was already kinda pissed due to me having to pull away from Blair, I soon turned my back to her which I hated to do but Nate was being more and more vocal about some crazy bitch at the club who wouldn't leave him alone.

It was after hearing Nate's name that I began to fastion my bra back together I then began to button my shirt back up once that was completely done I sat there for a second rehashing everything that just happened.

Nathaniel why don't you just tell her to fuck off... "he was starting to drive me insane and all I wanted to do was get back to the sexy little petite in my bed" Yeah I get that but you and I both know how this game work, let her know that you don't fool with any girl more then once and send her ass on her way... one & done my man... its that simple.

Hearing Chuck's words instantly made me come off whatever high I had been on before. It would be a lie to say that I didn't know this before but I guess herein him say it right now made it even more clearer to me... that's right Chuck only fooled with a girl once and then after that he ditched them. He got me to orgasm for him did that too mean that he was threw with me as well. Who was I kidding to even think that someone like me would even excite him, I mean I didn't even give him half of what other girls give him not to mention half those girls looked ten times better then I do.

Listen Nathaniel I will be by later okay... but I have to get off so talk to you later. "after that I quickly hung up the phone and turned back around to a very much dressed Blair Waldorf setting on my bed" Hey what... when did you decide to get dressed?

All uh I uh... didn't want to keep you held up or anything... "looking at him and smiling, trying to reassuring him and myself that everything okay" I mean I heard Nate he seemed to be a bit frantic and all is everything okay with him?

Yeah.. he's fine.. there is just some obsessed chick that wont leave him alone... "I began to laugh remember what Nate had said"

Oh... "I put on my best fake laugh as possible"

Yeah its quit stupid really... I mean if he didn't insist on talking to half the girls he fools around with after the deed is pretty much done he wouldn't be in this problem. This is why after I'm threw with whoever is my entertainment at that time I send them on their merry fucking way. So things like that doesn't happen... but you know Nate... "rolling my eyes, I then see her begin to move off the bed"

Oh yeah... "fake laughing again" Some girls can get the wrong picture after all... especially if he seemed overly friend even after they have there fun.

Yeah... "watching her body language I noticed instantly she seemed to be almost closed off from how she was before." Hey uh where are you going?

I... I was just going to head on out... I mean Nate obviously needs you and well I don't want you to think you have to hang out with me or anything I mean... don't feel like you owe me that or anything. I know you would much rather be on your way partying it up with your friends and stuff.

I'm sure they will be fine... I mean if you want to stay longer I don't care to entertain you.

"hearing the word entertain made his words resurface in my mind once more, I knew I needed to get away before he would reject me and send me on my way" I umm... I'm feeling kinda tired, plus I have loads of homework to do and stuff.

Well hey I can help you... I mean I've pretty much taken all those courses already you know.

No... you don't need to do that... besides its a three day weekend anyways & I know you probably want to get your partying started early... besides its nothing that I cant handle I promise. "I smiled at him before going to collect my jacket from the floor"

Well if you insist "not wanting to pressure her into staying if she didn't want to any longer, even though I found myself disappointed that she wanted to leave already. For some reason all I wanted to do was kiss her again and hold her body next to mine, maybe she wasn't into this whole new experience as much as I thought she was, watching her walk towards the door left me feeling almost lonely inside for some reason. But before she left she turned to me and spoke"

Chuckkk... "even though I knew I would never be what he wanted, I still wanted him to know what tonight meant for me. Seeing his head raise and his eyes meet mine I knew I had his full attention" Thanks... for tonight... It was everything I've ever wanted just so you know, the way you took your time with me. Between the gentleness yet agility you showed to my body tonight... It truly was amazing, your like this Sex God that I have had to opportunity to let pleasure me. I just want you to know that I will never forget what you did for me today. "I saw his eyes grow wide at my confession which made me smile and with that I turned to leave"

* * *

Only after she left did I let her words sink in even more, I guess I was wrong again.. she seemed very much into it, she even called me a Sex God... which made me chuckle slightly now but smile at the same time. Today had really been amazing for her so much so that she would never forget it... and If I was being honest with myself right now then I can honestly say without a doubt that I too would never forget today. The way she felt, looked, and the taste which made me close my eyes taking it all in once more.

Later that night Nathaniel showed up at my house where we proceeded to toke up a bit once we were completely high my mind began to replay everything of that day from finding her hiding in the kitchen to her confession of never having an orgasm to me offering. Undressing her kissing her seeing her perfect little body under mine the look on her face as I brought her to then over that wall to passion and pleasure she'd never felt to the taste of her on my fingers that still seemed to amaze me still yet and made me want her all that more.

Aye man... do you ever hate how we treat girls sometimes... "Nate spoke up interrupting his friend who seemed deep in thought"

I'm not sure I know what you mean Nathaniel... "why was he bringing up this for"

Well I mean earlier on the phone when you told me to stick with the plan... you know when you told me to tell he to fuck off... and that we only fool with a girl once and that was it... there pretty much dead to us.. I mean why does it have to be only once.

Nathaniel... I didn't... "thinking back to the conversations at hand it was then I realized everything that had come from my mouth and then some. Blair had overheard the words I said to Nate pretty much telling him that we don't fool with same girl twice, one and done. Not to mention what I told her personally after I hung up with Nate. Telling her about how after I'm done with a girl I send them on there way, that once there entertainment is threw with then I too and done with them. How it was stupid to talk to the girl after, did I seriously say all of that to her. I was starting to feel sick to my stomach its no wonder she was basically racing to get out of my room.

Nathaniel you might be right... or at least right about some girls anyways... " Blair was clearly one of those girls, she didn't deserve to be treated like those girls she was something else... something special I might have to say or at least she seemed that way to me. She practically entrusted me with the one thing no one had ever been able to touch and I pretty much insulated not directly to her of course but let her know my way of thinking which in turn made her think she was one of those girls when that couldn't be further from the truth. I quickly got up and grabbed my phone knowing I had her number already in my contacts, I needed to let her know that I still wanted to see her around that she was nothing like any of those girls"

**Hey B, just thought id let you know that I'm thinking about you right now -CB**

**Really?... umm that's surprising. But if its any constellation I too have been think about today also! -BW**

**Yes I don't think it will ever leave my mind, your are forever ingrained in my brain Waldorf :) -CB**

**LOL... your silly Bass... I'm sure It will soon be replace with whoever your next entertainment is. -BW**

**Never, and just so were clear you were never entertainment for me Blair. I genuinely liked what time we spent together today. -CB**

**Well then.. maybe we should spend a bit more time with one another then? -BW**

**Absolutely! how about tomorrow? Brunch say around 11:30ish? -CB**

**Brunch it is... :) see you then Bass. Night -BW**

**Night Beautiful! ;) -CB**

After walking to my room it was then I noticed something laying in the floor by my bed, bending down I noticed right away what it was, grasping the purple lace in my hands I couldn't help but smile even more it made me think about every single things that transpired between us that day, and even though I still didn't know what that might be I still found myself getting overly excited about meeting her for brunch. Climbing onto the bed and laying down I instantly clutched her panties as if someone would try to steal them threw the night, knowing they belonged to me not to mention a few other first of experiences too. Closing my eyes I found my mind was suddenly over took of images of Blair dancing through my mind.


End file.
